Petroleum distillate product



Patented Mar. 17, 1936 UNITED STATES PETROLEIM DISTILLATE PRODUCT Le Roy G. Story, Glenham, N. Y., assignor to The Texas Company, New York, N. Y., a corporation of Delaware No Drawing.

6 Claims.

This invention relates to petroleum distillate products, such as gasoline and kerosene, which normally tend to depreciate with respect to antiknock, color and gum properties on storage and 5 has to do particularly with the provision in the distillates of gum inhibitors, antioxidants or bleaching agents to impart a stability to the treated product and to remove objectionable color developed therein during storage.

It is well known that low boiling, light colored petroleum products, such as certain refined gasolines and kerosenes, particularly those containing cracked or unsaturated hydrocarbons, often be- 1 come disclored, decrease in anti-knock value, or

develop a gummy material under normal conditio'ns of storage and handling.

An object of the present invention is to provide a method and means of preventing or retarding Application October 27, 1933, Serial No. 695,513

and loss in anti-knock property in petroleum distillates.

Another object of the invention is to provide a method and means of bleaching or improving the color of petroleum distillates which have developed objectionable color on storage and to prevent or retard the recurrence of such discoloration.

I have found that the amino and the amino and hydroxy derivatives of phenones or mixtures thereof are valuable for the herein described ob- 1o jects and purposes of the invention. The phenones are a class of compounds having the formula o C5H50-R I in which R may be an alkyl or aryl radical. The invention may be more fully understood from the following illustrations which comprise some of the more important members of the class of compounds that come within the scope of the inventhe development of color and gummy substances tion: 20

(1 Aminoacetophenones o o ,0 0 cm 0 cm m a o-aminoacetophenone m-eminoacetophonone p-eminoacetophenono 0 0 0 0 0 cm 0 cm 0 cm 0-011:

HIN HaN H|N H NH 85.

I NH 2,3-diaminoaeetophenone 24-diaminoacetophenone 3,4-diaminoacetophenone 2.5-diamlnoaeetophenone 40 (2) Aminohydroxyacetophenones 4 0 O O 0 cm 0 -011. 0 011; BIN HN H0 2,3-aminohydroxyacetophenone Meminohydroxyaoetophenone aa-hydroxyamlnoecetophenone O O 0 y co1n 0 0m 0 0m 60 O 60 NH: on I NH: OH

56 ydr xyamin m p e 3, y my minoaeeto hanone 3,4-emlnohydroxyaoetophenone I mNO U mNO ONHa' NH: o-aminobenzophenone ordiaminobenzopbenone p-aminobensophenone 0 0 0 c o -c HsN RN Miaminobenm- 2 obenzopg-diaminobenzopbenone phenone phenone (4) Aminohydroxgbenzophenones 0 0 0 H|N OH EN N11, oraminohydmxybmsoza-eminohydroxyphenom praminohydroxybensophenone benzopbenona I Hs H0 H0 2,5-aminoh dm 3-h droxyamino' 2,5-hydtoxyamino' benzophezione 'beniopbenono bensopbenone In the foregoing illustrations no attempt is made to include all the possible amino or amino and hydroxy derivatives of the classes of compounds. One skilled in the art will immediately observe that there are other isomers, and also other amino or amino and hydroxy derivatives; for instance, triamino compounds, polyaminomonohydroxy compounds, or monoaminopolyhydroxy compounds, etc. are intended to be included in the invention. The invention is also intended to embrace the amino or amino and hydroxy derivatives of other homologues of acetophenone and benzophenone, such as propio-, butyro-, valero-, palmityl-, stearyl-, benzylphenones, etc. Sometimes it may be advantageous to have other substituent groups in the aromatic ring or rings, such as chlor, brom, methoxy, aikyl, aryl, etc. and these fall within the scope of the invention. Also I' may use compounds having an aryl radical comprising one or more condensed aromatic rings of the class of naphthalene, anthracene, etc.

The methods of preparation and the properties of the foregoing compounds are in general described in the literature to which reference is made particularly to Beilstein, Vol. III, and Richter, Vol. II.

In practicing the invention about 0.005 to 0.1% by weight of one or more of the inhibitors is incorporated into the oil to be treated. It is preferable to add the inhibitor to the freshly distilled product either by contacting the gasoline directly with the compound or the compound may be dissolved in the gasoline if desired; or, in case the solubility is low, by the aid of mutual solvents,

'such as acetone, alcohols, benzol, etc.

the various compounds is sumcient to stabilize effectively the color and gumming properties of unstable oils. In case the oil has gone off color, a material bleaching or reduction in color may often be effected and the restored color substantially stabilized according to the invention. Sometimes it is advantageous to use in conjunction with the inhibitors herein specified certain antioxidants of the prior art, such as pyrosalloi, thiocarbanilid, alpha-naphthol, etc.

As an example or the operation of the invention. there was dissolved in a gasoline showing about 200-300 mg. of gum per cc. by the Copper Dish Method (U. S. Bureau of Mines Method 530.1) 0.01% by weight of para-aminoacetophenone. The gum formation was reduced about 60-90% on the treated sample.

As a further illustration of the invention, to a cracked gasoline having a color of about 26 Saybolt universal was added 0.01% of diaminoacetophenone. Samples of the treated gasoline after exposure for one hour to sunlight lost about 5-10 points whereas the untreated sample lost about 15-25 points in color.

Obviously many modifications and variations of the invention, as hereinbefore set forth, may be made without departing, from the spirit and scope thereof, and therefore only such limitations should be imposed as are indicated in the appended claims.

I claim:

1. A distillate petroleum product of the class 2. A distillate petroleum product of the class of gasoline and kerosene, which normally tends to deteriorate and develop color and gum on storage, and containing diaminoacetophenone in suficient quantity to retard such deterioration and color and gum formation.

3. A method of treating cracked hydrocarbon distillates, of the class of gasoline and kerosene, which comprises subjecting the distillate to the action of p-aminoacetophenone.

4. A method of treating cracked hydrocarbon distillate, of the class of gasoline and kerosene, which comprises subjecting the distillate to the action of diaminoacetophenone.

5. A cracked gasoline, normally tending to deteriorate and form gum on storage, 'said gasoline containing a small amount of a gum inhibitor selected from the class of compounds having the following general formula:

wherein R. represents an alkyl group and X represents a hydrogen or amino group.

LE ROY G. STORY. 

